Disuccinimido dithiobispropionate

Base Information

• Chemical Name: Disuccinimido dithiobispropionate
• CAS No.: 57757-57-0
• Molecular Formula: C14H16N2O8S2
• Molecular Weight: 404.422
• Hs Code.: 29309090
• European Community (EC) Number: 260-931-5
• NSC Number: 328386
• UNII: EVY5D0U6SH
• DSSTox Substance ID: DTXSID00206449
• Nikkaji Number: J227.548A
• Wikidata: Q27277388
• Mol file: 57757-57-0.mol

Synonyms:3,3'-dithio(succinimidyl propionate);3,3'-dithiobis(N-hydroxysuccinimidylpropionate);3,3'-dithiobis(propionic acid hydroxysuccinimide ester);3,3'-dithiobis(succinimidyl propionate);3,3'-dithiodipropionic acid disuccinimide ester;3,3'-dithioldipropionic acid bis(N-hydroxysuccinimide ester);bis(2-((succinimidyloxy)carbonyl)ethyl) disulfide;disuccinimido dithiobispropionate;dithio bis(succinimidyl propionate);dithiobis((succinimidyl)propionate);dithiobis(succinimidyl-propionate);dithiobis(succinimidylpropionate);dithiobis(succinimidylpropionate), 35S-labeled;DSP cross linker;DTBSP;DTSP;Lomant's reagent;propanoic acid, 3,3'-dithiobis-, 1,1'-bis(2,5-dioxo-1-pyrrolidinyl) ester

Chemical Property of Disuccinimido dithiobispropionate

Chemical Property:

• Appearance/Colour: powder
• Melting Point: 128-133°C
• Boiling Point: 560.1 °C at 760 mmHg
• Flash Point: 292.6 °C
• PSA: 177.96000
• Density: 1.57 g/cm³
• LogP: 0.23820
• Storage Temp.: 2-8°C
• Solubility.: chloroform: 50 mg/mL
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 404.03480782
• Heavy Atom Count: 26
• Complexity: 552

Purity/Quality:

99.5% ^*data from raw suppliers

3,3''-Dithio(succinimidylpropionate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CCSSCCC(=O)ON2C(=O)CCC2=O
• Description: DSP Crosslinker is a cleavable crosslinker. It contains two terminal NHS ester moieties which can react with primary amines. The disulfide bonds can be cleaved via a reduction reaction using Dithiothreitol (DTT) reagent.
• Uses: 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) can be used as amine reactive homobifunctional cross-linking reagent, cleavable under mild conditions with hydroxylamine (pH 8.5, 3-6 h, 37oC) 3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) can be used in the crosslinking of intracellular proteins prior to cell lysis. 3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester) (DSP) has been used as a protein cross-linker.

Technology Process of Disuccinimido dithiobispropionate

There total 4 articles about Disuccinimido dithiobispropionate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

di(succinimido) carbonate (74124-79-1) + 3,3'-dithiobis(propionic acid) (1119-62-6) → 3,3'-dithiodipropionic acid, bis(succinimido) ester (57757-57-0)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.1002/jms.1854

Reference yield: 85.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3,3'-dithiobis(propionic acid) (1119-62-6) → 3,3'-dithiodipropionic acid, bis(succinimido) ester (57757-57-0)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2011.11.026

Reference yield:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3-mercaptopropionic acid (107-96-0) → 3,3'-dithiodipropionic acid, bis(succinimido) ester (57757-57-0)

Guidance literature:

Inert atmosphere;

DOI:10.1002/chem.201405747

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

3,3'-dithiobis(propionic acid)

di(succinimido) carbonate

3-mercaptopropionic acid

Downstream raw materials:

tyramine-DSP

C₈₀H₉₅N₁₅O₂₄S₂

C₅₃H₅₇N₇O₁₇S₂

C₅₆H₉₀N₂O₂₈P₂S₂

Refernces

• 1、 Tanaka, Kazuo,Kitamura, Narufumi,Chujo, Yoshiki. "Heavy metal-free 19F NMR probes for quantitative measurements of glutathione reductase activity using silica nanoparticles as a signal quencher". . p. 96 - 100. Retrieved 2012.
• 2、 Kim, Eunju,Kim, Dongwoo,Jung, Hyuntae,Lee, Jiyeong,Paul, Somak,Selvapalam, Narayanan,Yang, Yosep,Lim, Namseok,Park, Chan Gyung,Kim, Kimoon. "Facile, template-free synthesis of stimuli-responsive polymer nanocapsules for targeted drug delivery". . p. 4405 - 4408. Retrieved 2010.
• 3、 -. "DLL3-TARGETING MULTISPECIFIC ANTIGEN-BINDING MOLECULES AND USES THEREOF". . . Retrieved 2021/10/02.
• 4、 -. "NON-HUMAN ANIMAL HAVING HUMAN CD3 GENE SUBSTITUTED FOR ENDOGENOUS CD3 GENE". . . Retrieved 2018/07/30.